From a mental perspective burnout is definitely a real challenge in sales. I answered another question in how to handle burnout, as a career in sales is a marathon not a sprint. From a tactical perspective, one of the biggest frustrations I have experienced as an AE are constant book-of-business (BoB) or territory changes. AE's can really hit their stride when they can consistently work their BoB, and sudden, unexpected changes can be disruptive to productivity and revenue. Building a strong BoB is one of the hardest part of sales, once the foundation is set I like to give things time, watch reps cook and allows the “magic” to happen. *This is of course if the current BoB/Territory alignment is working.

1. Tell me about a deal that you were particularly proud of closing. How did you overcome obstacles to secure the deal? Proper Answer: The candidate should describe a specific sales challenge they faced, such as a tough negotiation or a difficult client objection. They should then explain the strategies they used to overcome the obstacle, such as active listening and creative problem-solving. 2. Tell me about the most challenging part of your current role and how you’ve overcome or mastered it. Proper answer: We’re looking to see an answer representative of a growth mindset. We want to hear examples of the individual overcoming adversity and sharing how they adapt and evolve in the face of challenges. 3. Tell me about a time when you received negative/constructive feedback from your manager, how you respond? Proper answer: This question aligns to the value of “learning faster through feedback”. How did the individual respond to the feedback and implement action (if any) in order to develop. 4. Explain concisely how your company creates value for customers. Proper answer: We’re looking to see if the individual can provide a short, easy to understand and memorable description of the product or solution. This is an indicator of strong communication skills. 5. Tell me about an opportunity that you lost that really hit hard. What did you learn? Proper answer: The answer should illustrate humility and resilience. Did they learn what to do next time to ensure a better outcome? Do they have an example of implementing the learnings?

Love this question, too. It's true. There are a few reasons: 1. You will always have outliers in a sales org. Sometimes a rep has a windfall and reaches quota without hitting KPIs, I've seen it. But the point of KPIs is the make success repeatable. 2. It gives your managers a tool kit to help coach and manage performance. 3. How do you eat an entire elephant? One bite at a time. Each KPI is a "bite" and we do best when faced with a big task (annual quota) to break it down to as small of pieces as we can.

I stole the idea of “WGLL” from Kevin Dorsey, who works across his leadership structure in sales teams to be maniacally focused on what good looks like, and work backwards from there. As such, I’ve rooted our metrics in support of WGLL - not from the perspective of “Amy & Bobby are the best, let’s have everyone do what they’re doing!”, but rather in using WGLL activities across my sales leaders to understand specific wins from the sales funnel and the supported customer experience to drive those metrics of success. For an example: we found that Amy is delivering a lot of value in the on-sites she’s running in her territory, let’s equip the team with her model (How far out she schedules, targeted personas, decks + sequences to set the meeting) and then hold them accountable to a number that Amy has driven to: 2 on-site meetings per month. Bobby is doing fantastic work top of funnel, and so we’ll capture what personas he’s engaging, what content and sequences he’s sharing, and communicate that as the KPI to the rest of the team.

When handling objections throughout the sales process, I generally advise first understanding the 'why' behind the objection/question, and then when you are comfortable with your understanding of the objection/question, then use a variation of the ARC Process (shown below) to manage the objection/answer. Understanding the Why behind an objection In sales you never want to answer questions that are not asked, and you never want to answer questions without knowing the intent behind the question/objection. If you have a suspicion as to the objection or the question, then I’d suggest normalizing it and better understanding it by reversing and framing your question back by saying, “Typically when a customer asks…it is because…to what extent would you say that is the case here?” Then once you fully understand the objection and the why behind it, you can use a variation of the ARC Process to overcome it: * Acknowledge: validate the objection/question and normalize it * Re-frame/Respond: clearly & succinctly provide your perspective * Confirm: then finally confirm that part of the conversation with a proposed path forward and validate that is acceptable with the prospect Example The prospect raises concerns over the cost of your solution, and you understand it's because they are also investigating a competitors who is cheaper but of lower quality. The ARC framework would sound something like this... (Acknowledge) Naturally, cost is always a consideration and I would be surprised if you hadn't raised it. (Re-frame) Our customers have shared that while we are a premium offering compared to other providers, the enhanced quality, speed, and performance of our solution not only provides better peace of mind, but also saves money over the long-term duration of the relationship, which makes it a sound investment. (Confirm) throughout our conversation, you've said that quality & speed are your top two criteria in choosing the right solution for you. If that's the case, is there any reason why you would not choose to invest in the best option?

With most of these questions, there isn't a one size fits all. Consider things like: * Company stage * Growth objectives * GTM strategy * Customer segmentation * Self serve vs. sales led * Compensation modeling AI has, of course, been a hot topic lately, begging the question of which roles will become obsolete. Personally, I think there will always need to be a human element. This AMA is a great example. If you wanted these answers you could find a generic response in Chat GPT vs. reading my response, but you are looking for the human experience aspect that ideally will provide you with more value. Below is a brief rundown of how I'd think through my org structure coming in at an earlier stage business. It's less about the actual title of the role and more about the function itself: * Inbound vs. outbound * Marketing * SDR * Partner/Channel * Customer acquisition * AEs * Customer retention * Onboarding Specialists * Customer Success/Account Management * Customer expansion * AE * Customer Success/Account Management * Customer reporting * Revenue Operations * Customer value * Sales Engineers * Solution Consultants * Leadership * Revenue * Sales * Customer Success * Revenue Operations Are all of these roles needed to get started? No. Figure out where you can create overlap in your roles by working backward on your bottoms up modeling for your revenue targets and determine how many people to need in order to achieve those goals. From here, you can uplevel the structuring into categories: * Functional: Think specialists vs. generalists. Core vs. overlay * Geographic: Location specific * Market Based: Industry/vertical specific * Product Sales: For larger organizations, this can be based on product SKU, bundle, etc. to drive certain revenue engines of the business

Welcome to the C-Suite. The people in this position have gotten there because they have really valuable perspectives to share and are often right. The best thing you can do being stuck in the middle is to be really clear about the decision(s) being debated as part of the proposed strategy, what the most salient points are that bolster or refute each argument and bring clarity on the decision(s) that need to be made and by when. Putting this into a document and asking folks to weigh in ahead of any meeting or debate can be a really valuable way to bring clarity to what's being proposed and ensure the sides are accurately represented. This exercise can also give both sides a chance to be sure they understand the alternative argument clearly and that their side is being represented in a way they would. It also gives the added benefit of bringing more voices into the fold giving them a chance to add data points or solicit perspectives that are important but might not yet be represented.

Many businesses focus on the effectiveness of a seller, where most of the attention should be. However, it can be very important to look at the effectiveness of those supporting your sellers, by measuring AE ramp time. If you can turn a 6 months period into say 4 months, you not only improve your revenue, but you can also improve the AE experience, leading to better employee satisfaction, higher referral rates, and lower attrition.

KPIs can certainly help to improve forecast accuracy. You can even build models to predict an outcome with a high accuracy. Deal velocity, pipeline coverage in different sales stages and forecast categories will help to predict the outcome. The more accurate data is available the better the models will become. This of course is on a pipeline level rather than on the deal level. No model can improve sales execution :-) This will become more difficult in unpredictable markets of course, however, still possible. Maybe with a higher range of accuracy.

Current Startup: * Team Composition: At my current startup, I’ve built a small but effective team. We currently have: * 2 Sellers * 1 Solutions Engineer * 1 Customer Success Manager * 1 Professional Services Team * My Role: I serve as the Head of Revenue, overseeing all these functions to ensure alignment and drive growth. * Future Growth Plans: * As we scale, I plan to grow the team to about five or six sellers, potentially adding another Solutions Engineer if capacity demands it. * I also envision adding three SDRs (Sales Development Representatives) with one manager, as well as expanding the Customer Success team to three members and the Professional Services team to two. * This structure should support a lead generation flow of about 100 leads per quarter, with an Average Selling Price (ASP) just under $30,000. Previous Experience: * Mid-Sized Teams: In my previous role at Clari, I managed between 7 and 14 sellers. However, I took on more responsibility when we acquired a business that I was asked to lead, soup-to-nuts. In this case, I had five SDRs under one manager, five direct-market sellers in India with another manager, and five direct-to-market sellers reporting directly to me in North America. In another role, I served as a General Manager, overseeing four regional managers, each responsible for a team of five sellers. Team Structuring Philosophy: My experience has taught me the importance of structuring sales teams to fit the company’s size, market focus, and growth stage. Future Expansion: * Scaling to Mid-Market and Enterprise: * As our business grows, particularly as we scale from 50 to 200 total employees, the sales team structure will evolve. * I anticipate segmenting the team further, with dedicated resources for Enterprise accounts (likely two sellers) and a separate team focused on the mid-market and SMB segments operating with a higher velocity approach. * This will require close collaboration with the product, engineering, and executive teams to ensure we’re aligned on strategy and execution. Long-Term Vision: * Complexity with Scale: I expect that as we continue to grow, the sales team will become increasingly complex. This will involve more specialized roles, additional management layers, and potentially further segmentation to address different market needs.